Resinous condensation product



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tented Jan. 7, 1941 y I 2,227,618- UNITED STATES PATENT} OFFICE,

RESINOUS CONDENSATIGN PRODUCT Werner zerweck and Max Schubert,Frankfortcn-the-MaIn-Fechenheim, to I. G. Farbenindnltrle Germany,assinlors Aktiengeleilschaft,

Franktort-on-the-Main, Germany ,No Drawing. Application March 21, 1939,Serial No. 263,184. In Germany March 22, 1938 5Glaims.

formaldehyde, or substances liberating aldehydes" with compounds of thegeneral formula:

H:N-("l NH arylen-E wherein arylen means a radical of the benzene andnaphthalene series and X stands for a mem. her oi the group consistingof 0 and S. The condensation reaction may he carried out in a neutral,acid or alkaline medium, in liquors or melts of an organic or morgahicnature, in solo tion or suspension, in the cold or in the hot.

Besides the above compounds other suiistaneee which can be condensedwith'aldehydee, such urea, thioui'ea, substituted areas, dicyandiamide,oulfonainides, earhoxylie acid amides, amines, phenols, aminodiandaminotriaoinee and the iilze may he added to the reaction mixtures Theresins ioimed may moreover be used in adminture with natural and otherartifieiai resins, such as phenol, urea, aniline, aminoti'iazine, alkydor isotonic resins.

According to the condensation conditions, par"- tieulariy to thequantity and the nature of the additional components the properties ofthe iiesine may be varied to a far-reaching degree.

In order to further illustrate our invention the following examples aregiven the parts being by Weight and all temperatures in degrees centieode.

Example 1 to parts by weight of 2-hydroxyphenyl-urea oi the iormuia:

Nil-G o-Nm nor a yellowish resin is obtained which is insoluble inorganic solvents. v

, lzamplez 10 parts of 4-hydroxyphenylurea oi the formula: p

' .NH--OO-NH| are mixed with about 100 parts of an aqueous formaldehydesolution oi! 30% strength and the mixture is slowly evaporated todryness to'about 90 to 100. The residue is maintained at thistemperature for some hours. The reaction prodnot is a resin soluble inaqueous caustic soda solution and insoluble in organic solvents. A verysimilar resin is obtained when replacing the 4- hydroxyphenylurea by thesame amount of 4- hydroxyphenyithiourea.

Example 3 parts oi 3-hydroxyphenylurea oi the formula:

- formed resin is hardened by shortly heating at When replacing theformaldehyde solution by t parts of benzaldehyde a similar resin of agood resistance to water is obtained.

Example 4 A mixture of parts of fl-hydroxyphenylthiourea or the formula:

NE-CB-NH:

' about 100 parts of an aqueous formaldehyde solution or strength and 1part of pyridine is evaporated to dryness on the water bath. The residueis heated for some hours at 90 to 100. A resin, insoluble in organicsolvents, is obtained.

Example 5 10 parts of l-hydromaphthylurea of the tormula: I

' mI-co-Nm V 188'imelting point and obtainable by decomposi. Resinouscondensation products obtained by condensing an aldehyde with a compoundof the general formula:

wherein arylene means a. radicle of the benzene and naphthalene seriesand x stands for a member of the group consisting o! O and S.

2. Resinous condensation products obtained by condensing formaldehydewith a compound of the general formula:

HaN-C-NH-aryhn-OH wherein arylene means a radicle of the benzene andnaphthalene series and 1! stands for a member of the group consisting ofO and 8.

3. A resinous condensation product obtained by condensing formaldehydewith 2-hydroxypheny1- urea of the formula:

' which resin is insoluble in organic solvents.

4. A resinous condensation product obtained by condensing formaldehydewith 3-hydroxypheny1- urea of the formula:

which resin is insoluble in organic solvents.

5. A resinous condensation product obtained by condensing formaldehydewith 3-hydroxyphenyithiourea of the formula:

. Nn-cs-NH,

which resinis insoluble in organic solvents.

zmwncx. -HAX SCHUBERT.

